TW409148B - Process for preparing nicotinamide - Google Patents
Process for preparing nicotinamide Download PDFInfo
- Publication number
- TW409148B TW409148B TW085113648A TW85113648A TW409148B TW 409148 B TW409148 B TW 409148B TW 085113648 A TW085113648 A TW 085113648A TW 85113648 A TW85113648 A TW 85113648A TW 409148 B TW409148 B TW 409148B
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- Prior art keywords
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- Prior art date
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- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title claims description 30
- 229960003966 nicotinamide Drugs 0.000 title claims description 14
- 235000005152 nicotinamide Nutrition 0.000 title claims description 14
- 239000011570 nicotinamide Substances 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 3
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 24
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims abstract description 8
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims description 90
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 81
- 229910021529 ammonia Inorganic materials 0.000 claims description 39
- 238000002360 preparation method Methods 0.000 claims description 38
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 34
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 239000001301 oxygen Substances 0.000 claims description 32
- 239000007789 gas Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 244000005700 microbiome Species 0.000 claims description 23
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims description 22
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000011049 filling Methods 0.000 claims description 16
- 230000003647 oxidation Effects 0.000 claims description 15
- 238000007254 oxidation reaction Methods 0.000 claims description 15
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 12
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 11
- 230000002079 cooperative effect Effects 0.000 claims description 10
- 239000004408 titanium dioxide Substances 0.000 claims description 10
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 9
- 230000000813 microbial effect Effects 0.000 claims description 9
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 9
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 9
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 9
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 8
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 241000316848 Rhodococcus <scale insect> Species 0.000 claims description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- 239000010936 titanium Substances 0.000 claims description 7
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 6
- 229910001935 vanadium oxide Inorganic materials 0.000 claims description 6
- 239000012467 final product Substances 0.000 claims description 5
- FMCKWHVKSJTVHU-UHFFFAOYSA-N C1(=CC=CC=2C3=CC=CC=C3CC12)C(CN)CCCN Chemical compound C1(=CC=CC=2C3=CC=CC=C3CC12)C(CN)CCCN FMCKWHVKSJTVHU-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000003798 microbiological reaction Methods 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 229910052720 vanadium Inorganic materials 0.000 claims 3
- 229910052726 zirconium Inorganic materials 0.000 claims 3
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 2
- WZXJVSMLELGKTQ-UHFFFAOYSA-N 3-methyl-2h-oxete Chemical compound CC1=COC1 WZXJVSMLELGKTQ-UHFFFAOYSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 238000009434 installation Methods 0.000 claims 2
- 150000002978 peroxides Chemical class 0.000 claims 2
- 239000010970 precious metal Substances 0.000 claims 2
- 229910052710 silicon Inorganic materials 0.000 claims 2
- 239000010703 silicon Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 229910052719 titanium Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical group O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 claims 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- HSDSMVWMLHEKNR-UHFFFAOYSA-N ClN.CN1CCCC1C1=CC=CN=C1 Chemical compound ClN.CN1CCCC1C1=CC=CN=C1 HSDSMVWMLHEKNR-UHFFFAOYSA-N 0.000 claims 1
- 241000270666 Testudines Species 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 abstract description 9
- 230000008569 process Effects 0.000 abstract description 5
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- JJQHTLAUSSTREE-UHFFFAOYSA-N hexane-3,3-diamine Chemical compound CCCC(N)(N)CC JJQHTLAUSSTREE-UHFFFAOYSA-N 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- -1 Amberlite) Chemical compound 0.000 description 5
- 239000011942 biocatalyst Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 241000187562 Rhodococcus sp. Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000036983 biotransformation Effects 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 235000015170 shellfish Nutrition 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000158504 Rhodococcus hoagii Species 0.000 description 2
- 241000187693 Rhodococcus rhodochrous Species 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 230000008092 positive effect Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- NJCWHFAIXRJJBP-XZBKPIIZSA-N (2S,3R,4R)-2,3,4,5-tetrahydroxy-2-[(1R)-1-hydroxy-2-oxoethyl]pentanenitrile Chemical compound OC[C@@H](O)[C@@H](O)[C@@](O)(C#N)[C@@H](O)C=O NJCWHFAIXRJJBP-XZBKPIIZSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- UHSVROPHFKRJIN-UHFFFAOYSA-N 2-methylcyclopentane-1,1-diamine Chemical class CC1CCCC1(N)N UHSVROPHFKRJIN-UHFFFAOYSA-N 0.000 description 1
- VOUJRNMURLYCFQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound CC(CN)CCCN.NCC(CCCN)C VOUJRNMURLYCFQ-UHFFFAOYSA-N 0.000 description 1
- OMUQVIKOMHDAEY-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CNCCC1.CC1CNCCC1 OMUQVIKOMHDAEY-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 240000006413 Prunus persica var. persica Species 0.000 description 1
- 241000271570 Rhea americana Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 101100242191 Tetraodon nigroviridis rho gene Proteins 0.000 description 1
- 229930003270 Vitamin B Natural products 0.000 description 1
- QOCJITIEZIWNLJ-UHFFFAOYSA-M [OH-].[O-2].[Eu+3] Chemical compound [OH-].[O-2].[Eu+3] QOCJITIEZIWNLJ-UHFFFAOYSA-M 0.000 description 1
- FRIKWZARTBPWBN-UHFFFAOYSA-N [Si].O=[Si]=O Chemical compound [Si].O=[Si]=O FRIKWZARTBPWBN-UHFFFAOYSA-N 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- IBAHLNWTOIHLKE-UHFFFAOYSA-N cyano cyanate Chemical compound N#COC#N IBAHLNWTOIHLKE-UHFFFAOYSA-N 0.000 description 1
- 125000006159 dianhydride group Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- JVQUBHIPPUVHCN-UHFFFAOYSA-N hexane-1,2-diamine Chemical compound CCCCC(N)CN JVQUBHIPPUVHCN-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- NFVUDQKTAWONMJ-UHFFFAOYSA-I pentafluorovanadium Chemical compound [F-].[F-].[F-].[F-].[F-].[V+5] NFVUDQKTAWONMJ-UHFFFAOYSA-I 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- PBEXQBWLOXMXCU-UHFFFAOYSA-N pyridine-3-carbonitrile Chemical compound N#CC1=CC=CN=C1.N#CC1=CC=CN=C1 PBEXQBWLOXMXCU-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- FSPPEHRFPWPTQL-UHFFFAOYSA-N triazole-1-carbonitrile Chemical compound N#CN1C=CN=N1 FSPPEHRFPWPTQL-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
- C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Pyridine Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH309095 | 1995-11-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW409148B true TW409148B (en) | 2000-10-21 |
Family
ID=4248403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW085113648A TW409148B (en) | 1995-11-01 | 1996-11-08 | Process for preparing nicotinamide |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5719045A (fr) |
| EP (1) | EP0770687B1 (fr) |
| JP (1) | JP3911734B2 (fr) |
| CN (1) | CN1149199C (fr) |
| AR (1) | AR004260A1 (fr) |
| AT (1) | ATE212380T1 (fr) |
| AU (1) | AU700409B2 (fr) |
| BG (1) | BG63314B1 (fr) |
| BR (1) | BR9605410A (fr) |
| CA (1) | CA2187979C (fr) |
| CZ (1) | CZ290836B6 (fr) |
| DE (1) | DE59608641D1 (fr) |
| DK (1) | DK0770687T3 (fr) |
| EE (1) | EE03573B1 (fr) |
| ES (1) | ES2167503T3 (fr) |
| HU (1) | HU217689B (fr) |
| IL (1) | IL119402A (fr) |
| MX (1) | MX9605272A (fr) |
| MY (1) | MY119113A (fr) |
| NO (1) | NO318584B1 (fr) |
| PL (1) | PL185286B1 (fr) |
| PT (1) | PT770687E (fr) |
| RU (1) | RU2177474C2 (fr) |
| SI (1) | SI0770687T1 (fr) |
| SK (1) | SK283653B6 (fr) |
| TR (1) | TR199600857A2 (fr) |
| TW (1) | TW409148B (fr) |
| ZA (1) | ZA968485B (fr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5863750A (en) * | 1996-12-18 | 1999-01-26 | Cytec Tech Corp | Methods for the detoxification of nitrile and/or amide compounds |
| JP4476390B2 (ja) * | 1998-09-04 | 2010-06-09 | 株式会社半導体エネルギー研究所 | 半導体装置の作製方法 |
| US20050089987A1 (en) * | 2003-10-27 | 2005-04-28 | Lonza Ltd. | Polyacryamide beads containing encapsulated cells |
| US8324388B2 (en) * | 2006-02-15 | 2012-12-04 | Basf Aktiengesellschaft | Dehydrogenation process |
| KR101474573B1 (ko) * | 2006-08-08 | 2014-12-18 | 다우 아그로사이언시즈 엘엘씨 | 시아노피리딘을 함유하는 기상 반응 생성물의 켄칭 방법 |
| EP2305377A1 (fr) * | 2009-09-29 | 2011-04-06 | Lonza Ltd. | Catalyseurs pour la préparation de cyanopyridines et leur utilisation |
| EP2322273A1 (fr) | 2009-10-16 | 2011-05-18 | Lonza Ltd. | Catalyseurs pour la préparation de méthylpyridine |
| US8530664B2 (en) | 2009-10-16 | 2013-09-10 | Lonza Ltd. | Catalysts for the preparation of methylpyridine |
| EP2319833A1 (fr) * | 2009-10-16 | 2011-05-11 | Lonza Ltd. | Procédés et dispositifs pour la production de solutions aqueuses de cyanopyridines |
| EP2319834A1 (fr) * | 2009-10-16 | 2011-05-11 | Lonza Ltd. | Procédés et dispositifs pour la production de solutions aqueuses de cyanopyridines |
| CN102219734B (zh) * | 2011-05-10 | 2013-08-07 | 浙江爱迪亚营养科技开发有限公司 | 一种烟酰胺的制备方法 |
| CN103804284B (zh) * | 2013-01-07 | 2015-12-02 | 清华大学 | 用于制备3-甲基吡啶的系统 |
| CN104844539B (zh) * | 2014-02-17 | 2018-08-24 | 上海凯赛生物技术研发中心有限公司 | 一种哌啶的制备方法 |
| CN104762340A (zh) * | 2015-03-17 | 2015-07-08 | 安徽瑞邦生物科技有限公司 | 一种利用固定化细胞将烟腈转化为烟酰胺的方法 |
| HUE068578T2 (hu) | 2017-03-31 | 2025-01-28 | Merck Patent Gmbh | 5-Metil-(6S)-tetrahidrofolsav kristályos nátriumsója |
| WO2018178144A1 (fr) | 2017-03-31 | 2018-10-04 | Merck Patent Gmbh | Sel de sodium cristallin d'acide 5-méthyl-(6s)-tétrahydrofolique |
| CN112010802B (zh) * | 2020-08-13 | 2022-03-29 | 浙江新和成股份有限公司 | 3-甲基吡啶的连续制备方法 |
| CN111995572A (zh) * | 2020-08-19 | 2020-11-27 | 广州黛诗莎化妆品有限公司 | 一种美白祛斑加强型的烟酰胺结晶提取工艺 |
| CN117942976B (zh) * | 2024-03-27 | 2024-06-14 | 北京弗莱明科技有限公司 | 一种氨氧化反应催化剂及其制备方法与应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| SU1014228A1 (ru) * | 1981-05-06 | 1991-02-28 | Институт химических наук АН КазССР | Способ получени цианпиридинов |
| US5028713A (en) * | 1983-12-08 | 1991-07-02 | The Standard Oil Company | Ammoxidation of methyl substituted heteroaromatics to make heteroaromatic nitriles |
| US5179014A (en) * | 1985-01-08 | 1993-01-12 | Nitto Chemical Industry Co., Ltd. | Process for the preparation of amides using microorganisms |
| JPS61162193A (ja) * | 1985-01-08 | 1986-07-22 | Nitto Chem Ind Co Ltd | 微生物によるアミド類の製造法 |
| DD274631A5 (de) | 1987-09-18 | 1989-12-27 | Kk | Verfahren zur biologischen herstellung von amiden |
| JP2615819B2 (ja) * | 1988-04-28 | 1997-06-04 | 三菱瓦斯化学株式会社 | シアノピリジンの製造法 |
| US5258305A (en) * | 1991-09-13 | 1993-11-02 | Nitto Chemical Industry Co., Ltd. | Manufacture of optically active 2-phenylpropionic acid and 2-phenylpropionamide from the nitrile using Rhodococcus equi |
| GEP20012441B (en) | 1993-04-02 | 2001-05-25 | Lonza Ag | Process for Preparing 3-Methylpiperidine and 3-Methylpyridine |
| CZ338596A3 (en) * | 1994-05-23 | 1997-07-16 | Lonza Ag | Catalytic mixture for oxidative amonolysis of alkyl pyridines, process of its preparation and use |
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